1925 North Lincoln Avenue Chicago, IL 60614 +1 312 642 4700
If you are addicted to Monday Night Football and love Chicago-style pizza, Ranalli's is the place to dine. In each dining room, seasonal professional and college games play from the many televisions hanging from the restaurant ceiling. The menu features thick-crust pizza, sandwiches and barbecued baby-back ribs. The food is simple but good. In the summer, the sidewalk outside crowds with people waiting for tables in the beer garden. If the Bears could only make the playoffs.
632 North Dearborn Street Chicago, IL 60610 +1 312 266 1944
The building where Excalibur is housed opened in 1892. It was dubbed "the castle" and designed by Henry Ives Cobb, best known in Chicago as the architect for the Fisheries Building at the 1893 World's Fair. Today, "the castle" is home to a multi-level adult playground that features games, billiards, a club room that plays disco and "The Dome Room," which plays current music. This is a wildly popular nightspot and seems to draw "the beautiful people" from Chicago and the suburbs, as well as visiting celebs. Leave your flashy car with the valet, shine up your capped teeth and join in the fun.
140 East Walton Street Drake Hotel, Magnificent Mile Chicago, IL 60611 +1 312 787 2200
Tucked inside the Drake Hotel, Coq D'Or is one of the city's most elegant bars. It is not hard to believe that this dimly lit bar with its old world charm dates back to the early 1930s. Order up a martini, find a cozy table and bask in the swank of this experience. The menu features limited seafood selections, including a rich, flavorful clam chowder that is particularly satisfying on a cold day.
900 North Michigan Avenue 5th Floor Chicago, IL 60611 +1 312 266 2500
When hunger strikes during your Magnificent Mile shopping spree, enjoy a home-cooked meal at Frankie's 5th Floor Pizzeria, an Italian country abode nestled in one of the area's many shopping malls. Known for homemade pastas, thin-crust pizzas, chicken and seafood dishes, this is probably the only "home" that serves its meals in the living room, sun room, patio and barn. Scrumptious delights and relaxed ambiance, what more could you ask for!
20 West Division Street Chicago, IL 60610 +1 773 337 9080
The stockyards may have gone away, but another kind of meat market has taken shape in Chicago. Although the strip of division surrounding this bar is well known as a singles' Mecca, Butch McGuire's may be king of them all. The Irish decor is minimal, but people do not frequent Butch McGuire's for its charm; they come here to find someone charming. This place may well remind you of your college drinking days, for better or worse. The lonely often end up drowning their sorrows in cheeseburgers at the nearby Alumni Bar and Grill.
806 South Plymouth Court Chicago, IL 60605 +1 312 360 0234
Since 1947, Jazz Showcase has drawn considerable crowds with its top-notch acts, even after its much ballyhooed expulsion from the Blackstone Hotel a few years ago. Expect to pay for what you get. This is a first-class operation, from the tuxedoed staff down to the drink selection. On the walls are photos of jazz greats who have played at owner Joel Segal's clubs over the years. Take a moment to be impressed by the dazzling array of legends who have graced Chicago's classiest spot for live jazz.
11 East Hubbard Street Chicago, IL 60611 +1 312 642 6805
The nights are hoping at Andy's Jazz Club with music and great drinks in a dark, smoky interior. There is live music every night and on the weekends you can catch nationally known acts, such as Brad Goode. You can also have dinner or an appetizer while you enjoy the music. Try the Baked Brie Platter or the Seared Scallop Trio. This is a fantastic nightspot for great performances and tasty drinks.
601 North State Street Chicago, IL 60610 +1 312 266 7677
This will be an expensive evening out, but a real treat for those with a taste for good music and even better bubbly. Come for the delectable appetizers and desserts, and for the 20 different types of champagne by the glass. Stay for the music. Small combos and piano jazz are the mainstays here, so grab a seat in one of the plush booths and make yourself comfortable in the ultra-classy environment.
219 West North Avenue Chicago, IL 60610 +1 312 944 7020
A classic since it opened in 1958, the venerable "Ale House" hasn't changed a bit. The surrounding Old Town neighborhood is no longer as bohemian as it once was, but you will still find a motley and diverse crowd in here, from the crusty barmaids to the old drunk sitting next to you telling you everything you always wanted to know about shark fishing. Saddle up to the bar, order a Guinness, and keep your ears open. When Second City lets out, this place can get crowded with patrons and performers alike, making it one of the most fascinating and coolest bars in Chicago. A definite do-not-miss for the party crowd.
1616 North Wells Street Chicago, IL 60614 +1 312 337 3992
Not only a beloved Chicago showcase, Second City is now treasured by the world, as well. Many a legendary comedy career began here; perhaps you will catch tomorrow's star in tonight's revue. This is the birthplace of sketch comedy, the type of humor that spawned such shows as Saturday Night Live and The Kids in the Hall. In fact, many favorite SNL comedians got their start here. John Belushi, Bill Murray, Jerry Stiller and Elaine May are just a handful of those who went on to national fame. Be sure to check out all the photos on the wall while you wait to be seated - cabaret style, of course. The drinks are good, the price is right, the comedy and satire is unbeatable. This is an unforgettable end to an evening out in Old Town.